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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-09-08 16:37:37 UTC

Update Date

2022-03-07 03:18:05 UTC

HMDB ID

HMDB0112191

Secondary Accession Numbers

None

Metabolite Identification

Common Name

13-Hydroxyhexadecanoic acid

Description

13-hydroxyhexadecanoic acid belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 13-hydroxyhexadecanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0112191
     RDKit          3D
13-Hydroxyhexadecanoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
    6.8459    1.2468   -1.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5763    0.6446   -0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4356    1.4920   -1.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0705    0.9759   -0.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0555   -0.3310   -1.2415 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1107    0.7408    0.8117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9170    0.3519    1.5621 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1436   -0.8171    1.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2848   -0.6892   -0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3485   -2.0326   -0.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1622   -2.5072    0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2435   -1.5489    1.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1598   -1.3611   -0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2378   -0.3785    0.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2041   -0.1500   -0.7242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2443    0.8359   -0.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4976    2.0599    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8171    2.6296   -0.6762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5396    2.5684    1.4788 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6086    1.6739   -2.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6316    0.4729   -1.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2758    2.0324   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5257   -0.4116   -0.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6705    0.7577    0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4079    1.5252   -2.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5627    2.5141   -0.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525    1.5384   -1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4205   -1.0073   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4780    1.7316    1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9539   -0.0217    1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1525    0.2930    2.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1989    1.2706    1.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7894   -1.7308    0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4702   -1.1140    2.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    0.0011    0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163   -0.2487   -0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0153   -1.9752   -1.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4399   -2.7790   -0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5642   -2.7435    1.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6179   -3.5290    0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9046   -0.5867    1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910   -1.9700    1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6035   -0.8293   -0.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5967   -2.3143   -0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7098   -0.8560    1.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7793    0.5655    0.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6637   -1.0816   -1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6746    0.2997   -1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7093    0.3200    0.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9476    1.0070   -1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2457    3.4653    1.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 19 51  1  0
M  END


  Mrv1652309081718372D          

 19 18  0  0  0  0            999 V2000
    7.9480    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3783    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6638    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0927    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9493    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8072    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2349    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5217    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5204    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2362    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3770    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8059    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9506    5.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0914    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0914    4.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3796    5.4138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6651    4.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  2  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  2  0  0  0  0
 19 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0112191

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC(O)CCCCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H32O3/c1-2-12-15(17)13-10-8-6-4-3-5-7-9-11-14-16(18)19/h15,17H,2-14H2,1H3,(H,18,19)

> <INCHI_KEY>
RPTGBPWFRSJPOM-UHFFFAOYSA-N

> <FORMULA>
C16H32O3

> <MOLECULAR_WEIGHT>
272.429

> <EXACT_MASS>
272.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.12666710226898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-hydroxyhexadecanoic acid

> <ALOGPS_LOGP>
5.65

> <JCHEM_LOGP>
4.869864250666666

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.51627730533066

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019921291399

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2607805727112056

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
78.75309999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-hydroxyhexadecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0112191
     RDKit          3D
13-Hydroxyhexadecanoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
    6.8459    1.2468   -1.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5763    0.6446   -0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4356    1.4920   -1.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0705    0.9759   -0.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0555   -0.3310   -1.2415 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1107    0.7408    0.8117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9170    0.3519    1.5621 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1436   -0.8171    1.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2848   -0.6892   -0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3485   -2.0326   -0.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1622   -2.5072    0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2435   -1.5489    1.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1598   -1.3611   -0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2378   -0.3785    0.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2041   -0.1500   -0.7242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2443    0.8359   -0.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4976    2.0599    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8171    2.6296   -0.6762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5396    2.5684    1.4788 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6086    1.6739   -2.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6316    0.4729   -1.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2758    2.0324   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5257   -0.4116   -0.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6705    0.7577    0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4079    1.5252   -2.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5627    2.5141   -0.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525    1.5384   -1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4205   -1.0073   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4780    1.7316    1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9539   -0.0217    1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1525    0.2930    2.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1989    1.2706    1.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7894   -1.7308    0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4702   -1.1140    2.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    0.0011    0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163   -0.2487   -0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0153   -1.9752   -1.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4399   -2.7790   -0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5642   -2.7435    1.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6179   -3.5290    0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9046   -0.5867    1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910   -1.9700    1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6035   -0.8293   -0.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5967   -2.3143   -0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7098   -0.8560    1.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7793    0.5655    0.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6637   -1.0816   -1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6746    0.2997   -1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7093    0.3200    0.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9476    1.0070   -1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2457    3.4653    1.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 19 51  1  0
M  END

HEADER    PROTEIN                                 08-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-17         0                                  
HETATM    1  C   UNK     0      14.836  10.106   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.170   9.336   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.839   9.336   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.506  10.106   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.173  10.106   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.172   9.336   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.507   9.336   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.838  10.106   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.840  10.106   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.505   9.336   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.174   9.336   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.504  10.106   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.171  10.106   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      33.508  10.106   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.837   9.336   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.842   9.336   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      18.837   7.796   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      36.175  10.106   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      34.842   7.796   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   12                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   13                                                       
CONECT   11    9   14                                                       
CONECT   12    2   15                                                       
CONECT   13   10   15                                                       
CONECT   14   11   16                                                       
CONECT   15   12   13   17                                                  
CONECT   16   14   18   19                                                  
CONECT   17   15                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0112191
HETATM    1  C1  UNL     1       6.846   1.247  -1.308  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.576   0.645  -0.717  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.436   1.492  -1.157  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.070   0.976  -0.637  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.056  -0.331  -1.241  1.00  0.00           O  
HETATM    6  C5  UNL     1       3.111   0.741   0.812  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.917   0.352   1.562  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.144  -0.817   1.141  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.285  -0.689  -0.073  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.348  -2.033  -0.377  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.162  -2.507   0.776  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.243  -1.549   1.131  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.160  -1.361  -0.069  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.238  -0.379   0.419  1.00  0.00           C  
HETATM   15  C14 UNL     1      -5.204  -0.150  -0.724  1.00  0.00           C  
HETATM   16  C15 UNL     1      -6.244   0.836  -0.155  1.00  0.00           C  
HETATM   17  C16 UNL     1      -5.498   2.060   0.208  1.00  0.00           C  
HETATM   18  O2  UNL     1      -4.817   2.630  -0.676  1.00  0.00           O  
HETATM   19  O3  UNL     1      -5.540   2.568   1.479  1.00  0.00           O  
HETATM   20  H1  UNL     1       6.609   1.674  -2.308  1.00  0.00           H  
HETATM   21  H2  UNL     1       7.632   0.473  -1.470  1.00  0.00           H  
HETATM   22  H3  UNL     1       7.276   2.032  -0.676  1.00  0.00           H  
HETATM   23  H4  UNL     1       5.526  -0.412  -0.969  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.670   0.758   0.402  1.00  0.00           H  
HETATM   25  H6  UNL     1       4.408   1.525  -2.254  1.00  0.00           H  
HETATM   26  H7  UNL     1       4.563   2.514  -0.791  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.253   1.538  -1.037  1.00  0.00           H  
HETATM   28  H9  UNL     1       3.420  -1.007  -0.622  1.00  0.00           H  
HETATM   29  H10 UNL     1       3.478   1.732   1.287  1.00  0.00           H  
HETATM   30  H11 UNL     1       3.954  -0.022   1.066  1.00  0.00           H  
HETATM   31  H12 UNL     1       2.153   0.293   2.687  1.00  0.00           H  
HETATM   32  H13 UNL     1       1.199   1.271   1.556  1.00  0.00           H  
HETATM   33  H14 UNL     1       1.789  -1.731   0.954  1.00  0.00           H  
HETATM   34  H15 UNL     1       0.470  -1.114   2.016  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.617   0.001   0.205  1.00  0.00           H  
HETATM   36  H17 UNL     1       0.716  -0.249  -0.963  1.00  0.00           H  
HETATM   37  H18 UNL     1      -1.015  -1.975  -1.273  1.00  0.00           H  
HETATM   38  H19 UNL     1       0.440  -2.779  -0.662  1.00  0.00           H  
HETATM   39  H20 UNL     1      -0.564  -2.744   1.690  1.00  0.00           H  
HETATM   40  H21 UNL     1      -1.618  -3.529   0.517  1.00  0.00           H  
HETATM   41  H22 UNL     1      -1.905  -0.587   1.552  1.00  0.00           H  
HETATM   42  H23 UNL     1      -2.891  -1.970   1.980  1.00  0.00           H  
HETATM   43  H24 UNL     1      -2.604  -0.829  -0.862  1.00  0.00           H  
HETATM   44  H25 UNL     1      -3.597  -2.314  -0.355  1.00  0.00           H  
HETATM   45  H26 UNL     1      -4.710  -0.856   1.281  1.00  0.00           H  
HETATM   46  H27 UNL     1      -3.779   0.566   0.730  1.00  0.00           H  
HETATM   47  H28 UNL     1      -5.664  -1.082  -1.077  1.00  0.00           H  
HETATM   48  H29 UNL     1      -4.675   0.300  -1.582  1.00  0.00           H  
HETATM   49  H30 UNL     1      -6.709   0.320   0.683  1.00  0.00           H  
HETATM   50  H31 UNL     1      -6.948   1.007  -1.004  1.00  0.00           H  
HETATM   51  H32 UNL     1      -5.246   3.465   1.799  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5    6   27
CONECT    5   28
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9   33   34
CONECT    9   10   35   36
CONECT   10   11   37   38
CONECT   11   12   39   40
CONECT   12   13   41   42
CONECT   13   14   43   44
CONECT   14   15   45   46
CONECT   15   16   47   48
CONECT   16   17   49   50
CONECT   17   18   18   19
CONECT   19   51
END

HMDB0112191
     RDKit          3D
13-Hydroxyhexadecanoic acid
 51 50  0  0  0  0  0  0  0  0999 V2000
    6.8459    1.2468   -1.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5763    0.6446   -0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4356    1.4920   -1.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0705    0.9759   -0.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0555   -0.3310   -1.2415 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1107    0.7408    0.8117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9170    0.3519    1.5621 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1436   -0.8171    1.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2848   -0.6892   -0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3485   -2.0326   -0.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1622   -2.5072    0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2435   -1.5489    1.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1598   -1.3611   -0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2378   -0.3785    0.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2041   -0.1500   -0.7242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2443    0.8359   -0.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4976    2.0599    0.2085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8171    2.6296   -0.6762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5396    2.5684    1.4788 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6086    1.6739   -2.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6316    0.4729   -1.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2758    2.0324   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5257   -0.4116   -0.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6705    0.7577    0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4079    1.5252   -2.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5627    2.5141   -0.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525    1.5384   -1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4205   -1.0073   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4780    1.7316    1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9539   -0.0217    1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1525    0.2930    2.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1989    1.2706    1.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7894   -1.7308    0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4702   -1.1140    2.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6172    0.0011    0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163   -0.2487   -0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0153   -1.9752   -1.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4399   -2.7790   -0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5642   -2.7435    1.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6179   -3.5290    0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9046   -0.5867    1.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910   -1.9700    1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6035   -0.8293   -0.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5967   -2.3143   -0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7098   -0.8560    1.2807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7793    0.5655    0.7302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6637   -1.0816   -1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6746    0.2997   -1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7093    0.3200    0.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9476    1.0070   -1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2457    3.4653    1.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 19 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
13-Hydroxyhexadecanoate	Generator
16:0(13-OH)	SMPDB, HMDB
13-hydroxypalmitic acid	SMPDB, HMDB
13-hydroxyhexadecanoic acid	SMPDB
13-Hydroxypalmitate	Generator, HMDB

Chemical Formula

C₁₆H₃₂O₃

Average Molecular Weight

272.429

Monoisotopic Molecular Weight

272.23514489

IUPAC Name

13-hydroxyhexadecanoic acid

Traditional Name

13-hydroxyhexadecanoic acid

CAS Registry Number

59642-39-6

SMILES

CCCC(O)CCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C16H32O3/c1-2-12-15(17)13-10-8-6-4-3-5-7-9-11-14-16(18)19/h15,17H,2-14H2,1H3,(H,18,19)

InChI Key

RPTGBPWFRSJPOM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Hydroxy fatty acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.65	ALOGPS
logP	4.87	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	78.75 m³·mol⁻¹	ChemAxon
Polarizability	35.13 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	170.745	31661259
DarkChem	[M-H]-	170.881	31661259
DeepCCS	[M+H]+	170.14	30932474
DeepCCS	[M-H]-	166.121	30932474
DeepCCS	[M-2H]-	203.726	30932474
DeepCCS	[M+Na]+	179.423	30932474
AllCCS	[M+H]+	175.5	32859911
AllCCS	[M+H-H2O]+	172.4	32859911
AllCCS	[M+NH4]+	178.3	32859911
AllCCS	[M+Na]+	179.2	32859911
AllCCS	[M-H]-	173.3	32859911
AllCCS	[M+Na-2H]-	174.4	32859911
AllCCS	[M+HCOO]-	175.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
13-Hydroxyhexadecanoic acid	CCCC(O)CCCCCCCCCCCC(O)=O	3320.6	Standard polar	33892256
13-Hydroxyhexadecanoic acid	CCCC(O)CCCCCCCCCCCC(O)=O	2050.4	Standard non polar	33892256
13-Hydroxyhexadecanoic acid	CCCC(O)CCCCCCCCCCCC(O)=O	2164.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
13-Hydroxyhexadecanoic acid,1TMS,isomer #1	CCCC(CCCCCCCCCCCC(=O)O)O[Si](C)(C)C	2229.5	Semi standard non polar	33892256
13-Hydroxyhexadecanoic acid,1TMS,isomer #2	CCCC(O)CCCCCCCCCCCC(=O)O[Si](C)(C)C	2263.4	Semi standard non polar	33892256
13-Hydroxyhexadecanoic acid,2TMS,isomer #1	CCCC(CCCCCCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2283.1	Semi standard non polar	33892256
13-Hydroxyhexadecanoic acid,1TBDMS,isomer #1	CCCC(CCCCCCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	2482.1	Semi standard non polar	33892256
13-Hydroxyhexadecanoic acid,1TBDMS,isomer #2	CCCC(O)CCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2500.8	Semi standard non polar	33892256
13-Hydroxyhexadecanoic acid,2TBDMS,isomer #1	CCCC(CCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2749.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 13-Hydroxyhexadecanoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00bj-9452100000-e6451042a7acf01bb39f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13-Hydroxyhexadecanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9520000000-64bab93cf39d5eb55dc4	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13-Hydroxyhexadecanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 13-Hydroxyhexadecanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Hydroxyhexadecanoic acid 10V, Positive-QTOF	splash10-0a4i-0090000000-b3f1e51cc44b512552f9	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Hydroxyhexadecanoic acid 20V, Positive-QTOF	splash10-0a4r-3490000000-d687ffc6b2d9536dfa67	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Hydroxyhexadecanoic acid 40V, Positive-QTOF	splash10-0006-9710000000-45e19f96c6980e883090	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Hydroxyhexadecanoic acid 10V, Negative-QTOF	splash10-00di-0090000000-183919dcc4438b1c4358	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Hydroxyhexadecanoic acid 20V, Negative-QTOF	splash10-0uk9-1090000000-d59b8ee054af2ddfee69	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Hydroxyhexadecanoic acid 40V, Negative-QTOF	splash10-052f-9120000000-250b88f489cd32526a03	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Hydroxyhexadecanoic acid 10V, Positive-QTOF	splash10-0ab9-2290000000-6c2d651616524bb2c80b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Hydroxyhexadecanoic acid 20V, Positive-QTOF	splash10-0a4i-9630000000-36fa0ce3333bae4eb82d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Hydroxyhexadecanoic acid 40V, Positive-QTOF	splash10-0a4m-9100000000-6efb6fff2c3309142759	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Hydroxyhexadecanoic acid 10V, Negative-QTOF	splash10-00di-0090000000-8d7f9faa50e28069cb98	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Hydroxyhexadecanoic acid 20V, Negative-QTOF	splash10-0uk9-0090000000-a25dece7a168febdd6aa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 13-Hydroxyhexadecanoic acid 40V, Negative-QTOF	splash10-0006-9450000000-84e053500a97bd289e0f	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15569769

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Yore MM, Syed I, Moraes-Vieira PM, Zhang T, Herman MA, Homan EA, Patel RT, Lee J, Chen S, Peroni OD, Dhaneshwar AS, Hammarstedt A, Smith U, McGraw TE, Saghatelian A, Kahn BB: Discovery of a class of endogenous mammalian lipids with anti-diabetic and anti-inflammatory effects. Cell. 2014 Oct 9;159(2):318-32. doi: 10.1016/j.cell.2014.09.035. [PubMed:25303528 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 13-Hydroxyhexadecanoic acid (HMDB0112191)

MOL for HMDB0112191 (13-Hydroxyhexadecanoic acid)

3D MOL for HMDB0112191 (13-Hydroxyhexadecanoic acid)

3D SDF for HMDB0112191 (13-Hydroxyhexadecanoic acid)

3D-SDF for HMDB0112191 (13-Hydroxyhexadecanoic acid)

PDB for HMDB0112191 (13-Hydroxyhexadecanoic acid)

3D PDB for HMDB0112191 (13-Hydroxyhexadecanoic acid)

SMILES for HMDB0112191 (13-Hydroxyhexadecanoic acid)

INCHI for HMDB0112191 (13-Hydroxyhexadecanoic acid)

Structure for HMDB0112191 (13-Hydroxyhexadecanoic acid)

3D Structure for HMDB0112191 (13-Hydroxyhexadecanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra